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Search results; Over 1,000 homes in Pine Plains

Top guest favourite
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
3 bedrooms, 3 beds, 2 private bathrooms
23–28 Nov
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5.0 out of 5 average rating, 62 reviews
Guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 286 reviews
Guest favourite
Barn in Pine Plains
The Nook - An Adorable Secret Get Away
1 bed, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 191 reviews
Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 171 reviews
Superhost
Room in Pine Plains
The Smithfield Room
1 bed, 1 bathroom
31 Oct – 5 Nov
4.75 out of 5 average rating, 12 reviews
Top guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 king bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 10 reviews
Home in Stanfordville
Chic Lakeside Oasis | Near Rhinebeck & Millbrook
3 bedrooms, 3 beds, 3 bathrooms
28 Sept – 3 Oct
New place to stay
Home in Pine Plains
Polo Field Family Home | Games & EV Charger
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
New place to stay
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed, 1 bathroom
28 Sept – 3 Oct
4.96 out of 5 average rating, 218 reviews
Top guest favourite
Guest suite in Red Hook
the farmhouse suite @barn & bike
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 457 reviews
Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds, 2 bathrooms
17–22 Sept
4.93 out of 5 average rating, 92 reviews
Top guest favourite
Room in Red Hook
Guest suite near Omega Institute and Rhinebeck
1 queen bed, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 44 reviews
Guest favourite
Farm stay in Town of Ancram
Private Farmstay & Forest Spa Near Hudson
2 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 409 reviews
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 111 reviews
Top guest favourite
Home in Red Hook
Taconic Hill-a modern retreat on 50 forested acres
4 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Pine Plains
Family home with pond
5 bedrooms, 5 beds, 4.5 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 25 reviews
Guest favourite
Flat in Red Hook
Secluded Hideaway Gem
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 55 reviews
Guest favourite
Home in Town of Ancram
Modern Scandinavian Farmhouse w/ Vintage Camper
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 70 reviews